Diacetone-D-glucose → 1,2:5,6-Bis-O-(1-methylethylidene)-alpha-D-allofuranose

HRID 25470

Reaktionsgleichung

Reaktionsgleichung von HRID 25470
[CH3:1][C:2]1([CH3:18])[O:6][C@@H:5]([C@H:7]2[O:11][C@@H:10]3[O:12][C:13]([CH3:16])([CH3:15])[O:14][C@@H:9]3[C@H:8]2[OH:17])[CH2:4][O:3]1.CS(C)=O.C(OC(=O)C)(=O)C>>[CH3:1][C:2]1([CH3:18])[O:6][C@@H:5]([C@H:7]2[O:11][C@@H:10]3[O:12][C:13]([CH3:16])([CH3:15])[O:14][C@@H:9]3[C@@H:8]2[OH:17])[CH2:4][O:3]1

Komponenten

3

Edukt 2

HCID 7067560Diacetone-D-glucoseHCID 86609981DMSO acetic anhydride

Produkt 1

HCID 71570541,2:5,6-Bis-O-(1-methylethylidene)-alpha-D-allofuranoseAusbeute 58 %

Versuchsvorschrift

The surprising finding according the present invention is that it is possible to carry out the oxidation of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose with DMSO/acetic anhydride in one pot with the subsequent reduction of the 1,2:5,6-di-O-isopropylidene-α-D-ribofuranose-3-ulose to form 1,2:5,6-di-O-isopropylidene-α-D-allofuranose (formula I). It is very surprising that the reduction can be carried out in the presence of the oxidation mixture. It is also surprising that it is possible to use this oxidation procedure in large scale (1 mole), and that the lowest reported amount of excess acetic anhydride (5 times) provides 58 % yield of recrystallised and analytical pure 1,2:5,6-di-O-isopropylidene-α-D-allofuranose.

Quellen und Nachweise

ORD-Eintrag
ord-70af49f9fb64449f8c4213e49877ea46
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858726B2

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